Every great wine region has its rules, and Tuscany's were close to sacred. Then, in the early 1970s, a handful of aristocrats and winemakers looked at those rules, poured themselves a glass, and quietly ignored them. What they made was so good the authorities had no category for it. They had to invent one. That is the story of the Super Tuscan, and it is still one of the most satisfying acts of rebellion in the history of wine.

The name sounds like a marketing invention, and in a sense it is. British and American critics coined it in the 1980s to describe a new breed of Tuscan red that was breaking every rule and charging grand prices to do it. Decades on, the Super Tuscans are no longer outlaws. They are among the most collected, most imitated and most expensive wines Italy produces. But the rebel spirit is still in the bottle, and understanding where it came from is the best way to choose one.

The rules they broke

To appreciate the mutiny, you have to understand what it rose against. For most of the twentieth century, Chianti was bound by law to a formula that insisted on a proportion of white grapes in a red wine, a hangover from an old recipe that made for thin, forgettable drinking. A wine that strayed from the rulebook, that used Cabernet Sauvignon, say, or matured in small French oak barrels instead of big old Tuscan casks, could not call itself Chianti. It was demoted to vino da tavola: table wine, the lowest classification on the shelf, the same label slapped on the cheapest plonk in the supermarket.

So that is exactly what the rebels became. In 1968, on the coast at Bolgheri, Mario Incisa della Rocchetta released a Cabernet-based wine he had been making largely for himself, inspired by the great reds of Bordeaux. He called it Sassicaia. A few years later, in 1971, the Antinori family, whose history in Tuscan wine stretches back more than six centuries, blended Sangiovese with Cabernet, matured it in barriques and released it as Tignanello. Both were technically table wines. Both were extraordinary. The world noticed, and the price followed.

So what is a Super Tuscan, exactly?

Here is the honest answer: there is no legal definition. A Super Tuscan is a high-quality red from Tuscany that was originally made outside the region's strict appellation rules, usually by bringing in international grapes such as Cabernet Sauvignon, Merlot or Syrah, and often by ageing in French oak. That is the whole idea. It is a philosophy, not a recipe.

The classifications eventually caught up with reality. In 1992 Italy created the IGT Toscana category, a respectable home for serious wines that did not fit the older rules, and in 1994 Bolgheri was granted its own DOC. Many Super Tuscans now carry these proper credentials. But the term stuck, because it describes something the paperwork never could: ambition, and a willingness to put quality above tradition.

Two camps, one spirit

If you are shopping for a Super Tuscan, it helps to know there are broadly two families. The first is the Bolgheri style, grown on the maritime gravels of the coast and built around Bordeaux grapes, Cabernet Sauvignon and Merlot: dark, structured and velvety, with the polish of a well-cut suit. Sassicaia is its figurehead. The second camp keeps Sangiovese, Tuscany's native soul, at its heart, and dresses it up with a little Cabernet and some French oak. Tignanello is the original and still the benchmark. One looks to Bordeaux. The other reinvents Tuscany from the inside.

The grape mix tells you how the wine will feel. A Bolgheri blend leans plush and black-fruited, all cassis and graphite and smooth power, a velvet jacket of a wine. A Sangiovese-led Super Tuscan keeps a brighter, more savoury edge, red cherry and dried herb and a mouthwatering lift that makes it one of the great partners for food. Neither is better. They are simply two routes up the same mountain.

Are they worth the money?

It is a fair question, because Super Tuscans are not cheap, and the famous names climb into serious money. The short answer is that the best of them earn it. These are wines made in small quantities, from low-yielding vines on prized sites, matured patiently in expensive oak and capable of ageing gracefully for twenty years or more. They are also genuinely scarce, which is why collectors chase them and auction houses adore them. But you do not have to buy at the very top to taste the quality. The category is deep, and some of its smartest value sits just below the icons, in the younger siblings of the great estates. That is where a curious drinker should begin.

Where to start

You do not need to spend the price of a weekend in Florence to understand what the fuss is about. The clever entry point is a wine like Guidalberto, made at Tenuta San Guido, the same estate behind Sassicaia. It is the accessible younger sibling: a Cabernet and Merlot blend with the estate's signature polish and a fraction of the wait. It happens to come in magnum, which is a generous and rather lovely way to introduce a table of friends to the style. Open it, decant it, and watch the room go quiet.

When you are ready for the wine that started it all, there is Tignanello. More than fifty years on, it remains the reference point: Sangiovese given grandeur, with the structure to age for a decade or two and the generosity to drink beautifully now. It is not an everyday bottle, and it is not meant to be. This is the wine you open when the evening deserves it, when the cold has properly set in and there is something slow-cooked on the table.

The season for it

Super Tuscans were built for exactly this time of year. These are cold-weather reds, wines that want roast meat, braised shin, a rib of beef, a board of hard aged cheese, the kind of long, candlelit dinners that autumn and the run-up to Christmas were invented for. Give them air; an hour in a decanter does wonders, especially for the younger vintages. Pour them a touch below room temperature, which in a centrally heated house means cooler than you think. And do not drown them in anything too delicate. They are grand wines, and they want grand food.

If you want to place these wines in the wider map of the country, from the perfumed Nebbiolo of the north to the volcanic reds of Sicily, our guide to the best Italian red wine is the natural next step.

The Super Tuscans began as a protest and ended as an institution, which is the fate of all the best rebellions. More than half a century after a few stubborn aristocrats decided the rules were beneath them, their wines sit among the most sought-after in the world. Choose one this autumn, give it a decanter and a proper dinner, and you taste exactly why: the moment Tuscany backed its own judgement over the rulebook, and got it gloriously right.